Ethanol → N-Boc-4-cyanophenylalanine-N-methylamide

HRID 1463548

반응식

HRID 1463548 반응식
[C:1]([NH:8][C@H:9]([C:19]([OH:21])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].FC1C(O)=C(F)C(F)=C(F)C=1F.[CH3:34][N:35]1CCOCC1.C(O)C>C(Cl)Cl>[CH3:34][NH:35][C:19](=[O:21])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]#[N:18])=[CH:15][CH:16]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

참가 물질

6

반응물 4

HCID 702EthanolHCID 79724-MethylmorpholineHCID 13041PentafluorophenolHCID 7020841N-(tert-Butoxycarbonyl)-4-cyano-L-phenylalanine

생성물 1

HCID 22851210N-Boc-4-cyanophenylalanine-N-methylamide수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-Boc-4-cyanophenylalanine (1.92 g, 6.6 mmol) and pentafluorophenol (2.43 g, 13.2 mmol) in CH2Cl2 (30 ml) at 0° C. was treated with 4-methylmorpholine (0.74 g, 7.3 mmol). After stirring the reaction mixture for 3 hours, 8M methylazine in ethanol (15 ml, 19.8 mmol) was added and the reaction mixture left to stir at room temperature for 16 hours. The solvent was removed under pressure, the residue dissolved in CH2Cl2 (50 ml) and washed with saturated sodium bicarbonate (2×50 ml) , 1M citric acid (2×50 ml) and brine (50 ml). The CH2Cl2 layer was dried over MgSO4 and the solvent removed under pressure to yield the title compound as a white solid (1.84 g, 92%).

후처리

  1. waitthe reaction mixture left
  2. stirringto stir at room temperature for 16 hours
  3. customThe solvent was removed under pressure
  4. dissolutionthe residue dissolved in CH2Cl2 (50 ml)
  5. washwashed with saturated sodium bicarbonate (2×50 ml) , 1M citric acid (2×50 ml) and brine (50 ml)
  6. dry with materialThe CH2Cl2 layer was dried over MgSO4
  7. customthe solvent removed under pressure

출처 및 근거

ORD 기록
ord-9949f6ba5f064ab3845911c82f62e8b6
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05300674

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